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1 article(s) from Govindan, Subramanian

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

Peter H. Seeberger,
Claney L. Pereira and
Subramanian Govindan

Beilstein J. Org. Chem. 2017, 13, 164–173, doi:10.3762/bjoc.13.19

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Graphical Abstract

Figure 1: Structure of the S. pneumoniae serotype 12F capsular polysaccharide repeating unit [15].

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Scheme 1: Retrosynthetic analyses of the S. pneumoniae hexasaccharide 1.

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Scheme 2: Attempted synthesis of mannosazide building block 15. Reagents and conditions: (a) levulinic acid, ...

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Scheme 3: Synthesis of mannosazide building block 18. Reagents and conditions: (a) TBSCl, imidazole, DCM, 0 °...

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Scheme 4: Synthesis of the reducing-end trisaccharide 3. Reagents and conditions: (a) TMSOTf, (CH₃CH₂)₂O/CH₂Cl...

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Scheme 5: Synthesis of monosaccharide building blocks 8, 9 and 26. Reagents and conditions: (a) acetic anhydr...

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Scheme 6: Synthesis of the non-reducing end trisaccharide 2. Reagents and conditions: (a) TMSOTf, CH₂Cl₂, −30...

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Scheme 7: Attempted synthesis of hexasaccharide repeating unit 36 via a convergent [3 + 3] glycosylation stra...

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Scheme 8: Linear assembly of fully protected hexasaccharide 51. Reagents and conditions: (a) DDQ, CH₂Cl₂/MeOH...

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Scheme 9: Global deprotection to furnish S. pneumonia serotype 12F repeating unit hexasaccharide 1. Reagents ...

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Published 25 Jan 2017

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